How many nights would you have for Cortona/Arezzo and Assisi area?

kyb, the first part adds up to 8 nights, so I assume 5-6 for Cortona/Arezzo/Assisi/Spoleto.

drkathej, check the driving times from Montepulciano to your destinations in southern Tuscany and Umbria. You might want to eliminate another hotel change and just stay in Montepulciano longer. I'd probably spend 3 nights in Siena to allow a day for a drive through Chianti, and then 4-5 nights (or whatever the number) in Montepulciano.

Are you arriving at and departing from the Florence airport? If so, consider renting the car on arrival and heading to San Gimignano (a little over an hour's drive). Drop the car somewhere in Tuscany or Umbria, take the train to Florence and spend the last nights there.

What time of year is this trip?

I don't recommend renting a car upon arrival in Italy and driving if you are flying transatlantic and will arrive jet lagged. I think you have a good plan to go to Florence first, without a car. But if you are flying from some other part of Europe, sure.

The pretty little Umbrian town of Montone is very conveniently located for visits to Cortona, Assisi and Spoleto. So I recommend staying there so you consolidate your hotel stays. In fact, you can see Cortona en route to Montone from the Tuscany area.

Because it is not necessarily fun to drive in an out of Arezzo (it's not hard, it's just not fun), I recommend extending your stay in Florence on night to see Arezzo by train.

To include a drive through the Chianti, you might consider reversing your trip, leaving for Florence and heading east, to do the eastern part of your tour first, and then coming back north through a western route, ending in San Gimignano.

Presuming you are flying in and out of Florence, this is how I would do your wish list:


Florence--4 nights (day trip to Arezzo)
Rent car, drive to Montone via the Chianti. Stay 3 nights in Montone with day trips to Spoleto and Assisi
Drive to Cortona for lunch, stay in southern Tuscan town for 3 nights
Drive to San Gimignano via Siena.

You probably have more nights than that....

Thanks for the suggestions. I think we will fly in and out of Rome as the flight to Milan or Florence gets in late. We can arrive in Rome at 11:15 AM and take the train to Florence. Since we will need to get back to Rome to return home, it makes sense to end in the more southern parts.
I am guessing that it would be good for us to stay in Montepulciano for the southern Tuscany area (as opposed to another town)? I will check out Montone also.

Have you looked at flights into Florence or Pisa? You could fly into one of them and home from Rome.

I haven't checked into Pisa but the flight into Florence itself arrives late (8 PM) and it may cost more than flying into Rome.
I am beginning to form more solid ideas and think we would go to Florence--3 nights, St. Gim... for 1 or 2, Siena for 3, Montepulciano(??? or other nearby town--) for 2 and then perhaps Montone. This will enable us to tour Florence, the Chianti area, the southern area and then Umbria.
Are there any hotel recommendations for these places? One of our priorities is to have good restaurants nearby so we don't have to drive in unfamiliar places at night. We like both town, city and country areas so we would be up for going to at least one place in the country.